With this week’s arrival of Toby Keith‘s new album, Bullets in the Gun, several members of the CMT.com staff began thinking about all that has happened since he released his first single, “Should’ve Been a Cowboy,” in 1993.

One of the great things about Keith is that it’s always been difficult to pin him down in terms of his music and his personal outlook. He’s his own man, and he really does make his music without worrying if something is too dramatic, comical, emotional or, on occasion, political. The songs listed below seem to reflect that attitude.

“American Soldier”
This song spent four weeks at No. 1 in 2003, yet it’s the one people tend to ignore when trying to define Keith on the basis of the hit he released the year before. Instead of the “boot in your ass” message of “Courtesy of the Red, White and Blue (The Angry American),” the patriotic theme of “American Soldier” focuses on the incredible sacrifices made by those in the military. Regardless of what you think about war, in general, and the story that continues to unfold in the Middle East, most of us have no firsthand experience of what that’s like. In his song, Keith tries to convey that from the perspective of someone who deals with those emotions every day. — Calvin Gilbert

“Beer for My Horses”
When I first heard the title “Beer for My Horses,” I’ll admit to half-expecting the quirky, tongue-in-cheek kind of song which Keith has proved to have an ear for in the past. I’ve always enjoyed “You Ain’t Much Fun” as one of those. Then I heard Willie Nelson was in it … and I was still unsure. But when you really get into it, “Beer for My Horses” offers a serious message in a very smart way. The major theme is a call for justice in modern times, but by evoking imagery from the Old West — saddling up a posse, stringing up the outlaws — it feels like a nostalgic song about the American spirit rather than a straight-up story. The part Nelson sings really goes a long way toward accomplishing that feel. — Chris Parton

“Does That Blue Moon Ever Shine on You”
I had enjoyed his previous singles, but this is the one that made me start thinking about the full potential he had as a songwriter. To the best of my knowledge, Keith is the only one who has ever recorded the song. I always thought a noncountry act would latch onto it. Granted, the world of pop music had changed dramatically by the time Keith released it as a single in 1996, but it’s one of those classic songs that could be arranged to suit anyone from a boy band to Tony Bennett. — Calvin Gilbert

“God Love Her”
On the surface, this song may seem like any other about a crazy teenage rebel child runaway who’s got a thing for bad boys. But there is a happy ending and a moral, which thrill me no matter how many times I’ve heard this song since it was released in 2008. And only a man like Keith could make it believable as he belts out the song from the first-person perspective of the bad boy. A bad boy with an ego big enough to put himself in the same line as God (“Oh, me and God love her”). When his gypsy life starts taking its toll, naturally, she saves his soul from the devil. No wonder God loves her. — Alison Bonaguro

“How Do You Like Me Now?!”
I’ve always heard you should be nice to everyone because you never know when other people are facing serious problems in life, and maybe you can brighten their day. The lesson learned in “How Do You Like Me Now?!” is be nice because you never know when they’re going to write a song calling you out for being a complete and utter jerk. I can’t stand being underestimated, so this no-nonsense anthem always makes me smile and puts a little fire in my belly. Frank Sinatra once said, “The best revenge is massive success.” If this is true, Keith continues to laugh all the way to the bank. — Stephanie Pendergrass

“I Love This Bar”
When a friend rented his upstairs bedroom to me when I was in my early 20s, I found myself living just six blocks from my favorite East Nashville bar, which quickly became my neighborhood hangout. There’s no telling how many nights I spent there with the winners and losers, chain smokers and boozers. These days I live a few miles farther out, and I’m more of an early-bird than an all-nighter, but whenever my friends and I feel like a night out, mmm-mmm-mmm-mmmm-mmmm, I still love that bar. — Craig Shelburne

“Me Too”
Not exactly the romantic phrase a girl dreams about hearing the first time she reveals her feelings for her man. But in this 1996 hit, Keith explains that a guy can’t always say it like he can show it. Phrases like “it might go unsaid, but it won’t go undone” reassure and help make that shortage of words a little clearer. “I hope you know what I mean when I say, ‘Me too.’” Well, now I do. Thanks, Toby. — Andrea Graff

“My List”
He veered off into some poetic territory on this one, and I’ll be damned if this song doesn’t have one of the most important messages in all of country music. One about making sure you don’t fill your to-do list with so many trips to the hardware store that you don’t have time for the important things. There are a couple clichés in the mix, like playing catch and giving your gal a kiss, but if everyone put “laugh ’til it hurts,” “put an extra five in the plate at church” and “look up a old lost friend” on their lists, the world would be a better place. I love the piano on the recording, and when it’s warranted, as it is in this meaningful of a song, I am crazy about the reprise of the opening line: “Under an old brass paperweight is my list of things to do today” at the end. — Alison Bonaguro

“We Were in Love”
I think this song could easily have been titled, “We Were in Lust.” Turn back the clock to the first time you remember falling head over heels. The butterflies, weak in the knees, time-standing-still sensations are all there. It’s summer. It’s Friday. You’re young and life’s carefree. With lines like “fire down in your soul,” and “nights flowing like wine,” all those irresistible feelings rush to your mind like a brain freeze following a large slushy. Your hair’s blowing in the wind, you’re cruising in your first car … Close your eyes and let Keith sing you a song of nostalgia (but not necessarily of love). — Whitney Self

“Who’s That Man”
The impossible question of divorce is how to divide lives that have become so intricately knitted together. As Keith demonstrates in this dark, brooding song, no answer to that question comes without its toll. The narrator of “Who’s That Man” has lost every staple of his former life in the collapse of his marriage, and as if that weren’t bad enough, someone else is filling his shoes without any apparent hitch. Now he might as well be a ghost, lingering around the world he knows and loves — but incapable of ever returning to it. It’s a masterstroke of songwriting and performance that Keith manages to make the man’s unimaginable grief so palpable. — Dan Milliken